Navigating Singles Courtship in Middle Age: A Gentleman’s Guide to Attracting Women

Navigating Singles' Courtship in Middle Age: A Gentleman's Guide to Attracting Women

Can single men in their 40s and 50s still approach women they are interested in a nice and gentlemen-like way? Or is this approach outdated for their age?

Absolutely, do it old school. The charm of a well-mannered, gentlemanly approach has never gone out of style. Dating doesn't always require the internet. Go ahead, let your trousers off your legs figuratively—mind the pun, just jokes.

Empirical Observations from One’s Personal Experience

Yes, I am 42 in November, and one of my school friends’ sisters is 22. She's actually interested in a man like me, making for a 20-year age gap. My school friend, currently 39, wants me to be part of her life. With Christmas approaching, you could say I'll be mingling with her younger sister.

Imagine this: She works at the local supermarket. If she was constantly trying to get my attention, constantly talking to me, and eventually, I did start talking to her, the dynamics might shift. It's about timing and charm.

Modern Social Norms

The premise of your question is not entirely sound, according to my experience. In modern, industrialized societies—like North America—single men don't approach women at all. Note that I'm specifying "single men"; married men are allowed to approach women at will. In fact, I believe many marry just to feel free to approach women after marriage.

The stereotype persists in books, movies, and media that men are "gregarious" and seek women out. Women are often portrayed as being attracted to such men. However, in reality, such men are rare, and being gregarious is frowned upon. Social norms tend to punish those who exhibit such behavior as it goes against societal expectations.

The Two Contexts of Approach

Men could approach women in two primary contexts: cold and collegial. "Cold" means approaching someone with no introduction or history. This is generally seen as unsuitable, and society emphasizes the need for safety and mutual respect.

"Collegial" means approaching someone you know socially, asking them to meet outside their usual social setting. This is widely accepted. Women actually seem to prefer this scenario, provided the man doing the approach is someone they would like to approach spontaneously. This usually includes a very narrow and predictable category of men, typically those who have shown genuine interest in the past.

The Consequences of Misapproach

If a man gets it wrong, he could be labeled as either an overbearing lecher or a sad figure of lonely desperation. This judgment is particularly harsh on single men. If a married man acts similarly, he is often seen as harmless and flirtatious, with his behavior rated as acceptable because his current marriage is supposedly deficient.

Being discrete won’t mitigate these outcomes. If a man approaches a woman incorrectly and gets rejected, he might be seen as overbearing or lonely. But women say, "so what if he gets rejected? He's a man, he should be able to take that." While rejection itself is not enough to buffer such judgment, it certainly adds to the social consequences.

Conclusion

While the contemporary social norms make it challenging for single men in the 40s and 50s to approach women, it's not impossible. A gentlemanly approach, coupled with patience and understanding, can still be effective. The key is to be genuine and respect the woman's boundaries and preferences. Age is just a number, and timeless charm can cut through any stereotype.